Donald J. Trump ranked 156 on the coveted Forbes 400 list of wealthiest Americans in 2016 when he received just enough votes to become the President of the United States. At the time, his spectacular net worth clocked in at $3.7 billion, down from $4.5 billion in 2015 when he announced his campaign. Trump became the first billionaire to be elected president.
You have to admire his fantastic real estate investments. The properties, which hold a large share of his net worth, are as luxurious as they are pricey. How fabulous are his digs? His excessively gorgeous prime real estate ventures are something to behold. Let’s see what, exactly, is hidden inside Trump’s many, many fabulous mansions and skyscraper towers.
The Seven Springs Estate, Bedford, NY – $24 Million
This property, called Seven Springs, just 45 miles north of New York City, is a veritable palace. Set on 213-acres of rolling hills and orchards in Westchester, the 50,000-square-foot mansion has 60 rooms, two servant wings, and 15 bedrooms, plus 12 bathrooms. If they run out of room there, the property includes a Tudor-style, stone manor guest house with its own chapel that was built by ketchup magnate H.J. Heinz in 1919, named “Nonesuch.” (Trump will rent it to you for $10,000 a month).
The main mansion was also built in 1919, by Eugene Meyer—then President of the World Bank Group, owner of the Washington Post and, later, Federal Reserve Chairman. Meyer hired artist and architect Charles A. Platt to design it and commissioned Italian artisans to work on it. An indoor pool constructed completely of Italian white marble, one of three pools, highlights its luxury. Ever since Trump purchased the property in 1996, he began fighting to develop the 200-plus acres of pristine nature preserve into a golf course resort. His neighbors fought him off until he finally agreed to relinquish the plan.
Trump National Golf Course, Bedminster, NJ – $27.8 Million
This property is a favorite of Trump because he built it from the ground up. In 2002 he bought the 520-acre property, including the estate of John DeLorean of the DeLorean Motor Company, for around than $35 million. In 2004, the 36-hole golf course opened. He loves it so much, he chose to be laid to rest there inside a classical mausoleum, his final resting property. His plans for the family cemetery were approved in 2015. Since then he has considered relocating it to Florida, his other favorite estate. Located on the heart of New Jersey’s farm country, it’s a beautiful destination. Ivanka Trump held hers and Jared Kushner’s wedding there. Trump National Bedminster is a world-class golf course that is scheduled to host the 2022 PGA Championship and costs $350,000 to join. It’s a drop in the bucket for some of the celebrities and political elites who oft attend, Rudy Giuliani, President Bill Clinton, and former Yankees manager Joe Torre, to name a few. Membership includes use of the Heli-pad, in case the 45-minute drive from N.Y.C. is too long.
Reportedly, Trump rounded up the value of the property to $50 million on his federal documentation and saves on operating costs by hiring undocumented immigrants. The Trump Organization property also includes cottage homes for some of the Trump family members. Ivanka Trump and Jared Kushner love their cottage so much they’re extending it by 2,200-square-feet. Occasionally referred to as “Camp David North,” it’s one of the properties Trump prefers to use for official presidential business. Trump National Bedminster was also used as his transition team venue before the inauguration.
Trump Tower, Midtown Manhattan, NY – $323 Million
For years, this is where Trump called home. Inside Trump Tower on Fifth Avenue in Midtown Manhattan are the headquarters for The Trump Organization, space for Trump’s personal offices and his penthouse residence, taking up the top three floors of the 664-foot-high skyscraper. Trump designated this apartment as a home base up until security issues related to his new role as President made it impractical to reside in his extravagant 11,000-square-foot, high-rise condominium 58 floors in the sky. Even when he’s not home, it costs The City more than $1 million each day to protect the building. He misses it. With sweeping views of New York City’s Central Park, intricate marble carvings of Greek classical mythology, and columns and walls inlaid with 24-karat gold where family portraits hang, the only thing missing is him. Massive crystal chandeliers and classic art paintings adorn stunning ceilings. Furniture and style reflect the excessiveness of Louis XIV’s Palace of Versailles. The front door is inlaid with gold and diamonds. Naturally, his opulent condominium office and residence are a little larger if you ask Trump. For years he’s bragged that his Tower residence is 33,000-square-feet. City records show it’s 10,996-square-feet.
The Trump Organization built the tower in 1983. While his name is emblazoned upon the skyrise front entry, what he actually owns are the top three floors, housing, as well as the ground floor retail space—which has been virtually abandoned. Once lined with luxury retail like Harry Winston and Cartier, his foray into politics has had retailers going elsewhere. Nike left last year; only Starbucks and Gucci remain. Trump’s share of the Tower, in total, including retail space, is 244,000-square-feet! All told, it’s worth about $323 million.
The Mar-A-Lago Club, Palm Beach, FL – $160 Million
This national historic landmark built in 1924 by Post cereal heiress Marjorie Merriweather Post was bequeathed by her to the National Park Service hoping the property could be appropriated as a “Winter White House.” It didn’t work out. Maintenance costs were too high, and the estate was returned to the remaining Post family. But now, it seems, Post’s will for the property to be used by The White House has been fulfilled. Trump has already entertained two world leaders, Japanese Prime Minister Shinzo Abe and his wife in February of 2017 and Chinese leader Xi Jinping for two days to discuss international events in April of the same year. Last year in April, Trump hosted a two-day government summit with Prime Minister Shinzo Abe. Mar-a-Lago has become Trump’s weekend retreat of choice, it’s an opulent hangout. Heiress Post took care to build the mansion’s exterior walls with over three boatloads of stone from Genoa, Italy, and, imported 16th-century Roman busts to adorn the entrance hall. Trump managed to purchase the 128-room, 62,500 square-foot mansion, and 17-acre property for $8 million in 1985. His infamous real estate acumen scored a huge deal, Trump’s made over $100 million dollars on the property. He has developed a real affinity for the property, making it unclear if he’ll move his family cemetery plans to Palm Beach or leave it in Bedminster.
The Mar-a-Lago Club is exclusive, to say the least. There’s a $200,000 fee to join and annual dues of $14,000 to keep your membership. Members have access to the Beach Club and its pristine private beach, the Trump brand Spa and Salon, the formal and casual dining areas, a fitness center and the pool. Nonmembers may hold private events at Mar-a-Lago with access to the gorgeous grand ballroom. If you want to stay at the resort, it’s only $2,000 per night. A bargain considering you may run into the President of the United States!
Trump Winery, Charlottesville, VA – $34 Million
Trump Winery is set amongst the foothills of the Blue Ridge Mountains on 1,300 acres of rolling hills and stunning scenery. Snuggled up to none other than Jefferson’s beloved Monticello and sitting only a few miles from James Monroe’s Highland, it’s a fantastic property. The 227-acres of vines lining the estate make it Virginia’s largest vineyard. The good news is—we can visit. Swing by, taste some East Coast wines, dine on a bite of lunch at common folk prices. . . If you want to stay overnight it’s a relatively modest $349 bed and breakfast experience. Before Trump scored the deal, the property was called Kluge Estate Winery and Vineyard. John and Patricia Kluge owned and operated it. For perspective, in 1989, John Kluge was America’s richest person, according to Forbes. Trump purchased 200 acres surrounding the winery with his eye on the Kluges’ English manor house-style estate, as it had fallen into foreclosure. The bank alleged that Trump intentionally devalued the surrounding land by putting up “no trespassing” signs and allowing the property to become unsightly and overgrown to ward off buyers. End result, Trump snagged the land, including the 26,000-square-feet Albemarle mansion he coveted, for $3.6 million, a bargain discount from the bank’s $16 million foreclosure investment, and pocket change from the Kluge’s $100 million asking price only a year prior.
It’s easy to see how he earned his reputation as a shrewd real estate mogul. Afterward, he grandiloquently announced he owned the East Coast’s largest winery; however, the fact is another winery in the area doubles Trump Winery production. Trump owns the largest vineyard. Is it overly semantic to note the difference? It’s hard to overstate the grandeur of Albemarle House. The splendor of the 45-room mansion gushes with 1760-era Waterford crystal chandeliers, antique mantels carved from 150-year-old English oak, hand-painted ceilings and wallpaper, hand-carved brass fixtures. Outside you’ll find horse stables, a Heli-pad and a private chapel. For modern luxury, the estate includes billiards, a private movie theater, 24-hour fitness access, indoor hot tub and sauna, outdoor pool, croquet and bocce ball. Today, to show Trump is concerned about conflicts of interest, his son Eric operates Trump Winery and Patricia Kluge manages it. Once Trump was sworn in, he placed all his assets and The Trump Organization dealings into a Trust fund that his sons Eric and Donald Jr. manage. It’s not exactly clear whether it’s legal for presidents to run their businesses while in office, but he certainly veered off track from protocol—he’s the first president who chose not to divest. Days before his inauguration Trump explained his position at a press conference: “I could actually run my business and run government at the same time. I don’t like the way that looks, but I would be able to do that if I wanted to.” Others in his path have deemed it unsavory to profit from national duty calling it a conflict of interest, while Trump has a different perspective, boasting to Forbes in 2000, “It’s very possible that I could be the first presidential candidate to run and make money on it.” The point, in fact, the Trump Organization targets and hopes to break into a new market, the MAGA crowd, no matter their lower-class proclivities. Trump blurs the conflict-of-interest line. ‘What’s good for his business is good for American business, what’s good for American business is good for the country,’ meanwhile, he makes it “look” like he’s not running his business by handing that responsibility to his sons. The Albemarle estate bottom line? Trump made $30 million.
Le De Château Des Palmiers, St. Martin, West Indies – $15 Million
Built into Plum Bay’s shimmering, sprawling sandy beach, Le de Château des Palmiers is one of St. Martin’s most enviable Caribbean island estates. The 4.8-acre, 11-room villa and guest house are safely enclosed within an 8-foot-high walled-off section of the tiny half-French island. Once inside, you’ll be entranced by its shimmering marble, grand entrance. Walk outside to take in its immense pool and the gorgeous Caribbean Sea. Trump snagged this Island gem from a fellow businessman in 2013 for an undisclosed price. (It was listed for $19.7 million). In 2017 he listed it for $28 million with Sotheby’s International who declared on Instagram, in classic Trumpism style, “It’s huuuuuge!” It wasn’t selling. To entice he lowered it to $16.9 million a few months later.
Interest spiked as he was elected president by then (no conflict of interest here) but ultimately waned due to the prospect of the intense public scrutiny that would bombard a high-profile purchase. Meanwhile, he’s been raking in profits. With rates of up to $20,000 per night, rental income brought up to $1 million for the Trump Organization in 2017. Interested in visiting St. Moritz? Yes, you can! It’s publicly available on Airbnb. It’s one of the greatest mansions in the world, Trump said.
Marla Maples And Tiffany Trump’s Calabasas Custom Home
Tiffany Trump was only five when her mom moved them to the West Coast. Marla Maples and Donald’s union was Trump’s second failed marriage which ended abruptly as he moved on to model Melania Knauss. After the divorce, Marla decided to relocate from the busy bustling East Coast to quiet Calabasas in Southern California where Tiffany could have a “normal” childhood. The two spent Tiffany’s childhood years in their 5-bedroom, 6-bath, 5,700-square-foot home. Modest compared with most of Trump’s digs, the beautiful property situated atop the exclusive Mountain View Estates opens up to breathtaking sweeping views. It’s a fairly large property with a basketball court and a spectacular swimming pool that includes a swim-up bar with built-in bar stools. Not just that, but it also has an amazing water slide.
The million-dollar home was a two-million-dollar home by the time Marla sold it in order that she could be near Tiffany on the East Coast. Tiffany, who is an aspiring singer, is now attending law school at Georgetown University after having graduated from the University of Pennsylvania in 2016.
Donald Trump Jr.’s Luxury Apartments At The Sovereign
Donald Trump Jr. grew up inside the glitzy Trump Tower penthouse. When he married Vanessa Hayden in 2005 at the fabulous Mar-a-Lago, just ten months after "Papa" Trump married Melania, they first lived in Trump Place, but then called their apartment on the Upper East Side at The Sovereign, home. He purchased the exclusive adjacent apartments in a posh district of Manhattan for $2.71 million.
To make room for their five children, they bought a third adjacent unit for $1.5 million, gradually expanded their home. The Sovereign is a unique and elegant co-op apartment building that gives the family fantastic views of Long Island from their expansive 6,000-square-feet, 12th-floor digs. It’s uncertain who will be living there in the future. The couple announced their divorce in March of 2018.
Eric Trump’s Westchester And Trump Parc East Homes
Eric Trump created a penthouse suite by combining three apartment units at the top of Trump Parc East. The elegant home cost him just over two million dollars in total. However, he snagged the third unit of the flat from building developer, Donald Trump, for $350,000—half its listed price! (Thanks, dad). Towering over Central Park in the heart of Manhattan, views are sweeping and spectacular. Its 1904 architecture is as graceful as it is distinguished. Originally constructed as a hotel and performance center, Trump purchased the building in the 1980s and turned the flagging property into profitable condominiums. Inside the classy condos, large windows, vaulted ceilings, hardwood floors, and wood burning fireplaces add to the luxuriating sense of having escaped the city.
On weekends the family escapes the city in earnest. Eric, his wife Lara, and young son Luke head out to their lovely mansion in Briarcliff Manor, an exclusive village in Westchester County. Located nearby Eric’s favorite childhood home, and where he proposed to Lara, the Seven Springs estate, is the place they call home. Lara has said that it's their favorite place to be, and they head out to their mansion sanctuary every chance they get. She loves to go riding and hopes to get a horse of her own. It’s also in close proximity to Trump National Golf Club in Briarcliff Manor making it convenient for Eric Trump, as executive vice president of the Trump Organization, to keep an eye on the property. Eric also stops by his vineyard when he has time. Recently it won a Sweepstakes award from the 2019 San Francisco Chronicle Wine Competition for Trump Winery’s 2014 sparkling Monticello Blanc de Blanc. It’s doing well with Eric at the helm.
The Greenwich, CT Mansion
This gorgeous colonial mansion built in 1939 was acquired by Trump and his first wife Ivana for $4 million in the 1980s. Today it’s on the market for $45 million. When Ivana sold it in 1998, six years after their divorce, the new owners, financier Robert Steinberg and his wife Suzanne, paid $15 million for the palatial residence. Trump sure has a knack for scoring a deal on real estate! Needless to say, the new owners had to scale down the opulence, removing the gold-leafing and making it a more casual and livable abode.
The property is extravagant. It’s nearly 20,000-square-feet and built on six acres of manicured green into the end of the Long Island Sound peninsula. Docks dot the waterfront periphery of the property. It’s got an indoor pool, an outdoor pool, mini golf putting greens, a tennis court and a darling guest house. Set in the town of Greenwich, the 8-bedroom, 13-bath home is just 45 minutes from Manhattan. The best part? You can make it yours for $45 million.
The Scotland and Ireland Golf Resorts – $78 Million
Trump has a true affinity for Scotland, it’s his homeland—at least on his mom’s side. His mom, Mary Anne Trump, was born in Stornoway and lived there until she immigrated to America when she was 17. His affection for Scotland led him to his dream of developing two golf courses in Aberdeenshire. He even wanted to name the second golf course development after her saying, “My mother loved Scotland and I wanted to create a lasting tribute to her.” It would be called, The McLeod Course if it ever gets built. There is, however, the McLeod House namesake, a magnificent Scottish mansion at which one may stay, accommodating Aberdeen golf guests. In 2005 Trump purchased a 1,400-acre piece of rugged, green Scottish coastline and white dunes for about $12.6 million. Out of it, he created a world-class golf resort by 2012 and has been busy trying to push through the rest of his development plans. His Aberdeenshire neighbors have been unsupportive, often protesting, and his arrogant attitude has earned him a lot of defiance from the Scots.
In 2014 he grabbed the existing Turnberry golf resort, now called Trump Turnberry, his most prestigious and prized world-class golf course located on the other side of Scotland’s coast, for $59 million. So far, the Scottish investments have not enjoyed Trump’s trademark exponential profiting, both of his Scotland golf resort ventures lost money for three years straight, from 2014 to 2016. But things may be turning around. In 2018 revenues for Trump International golf resorts, including his Ireland golf property, doubled at Trump Turnberry and posted a profit in the contested Aberdeen, increasing from $3.2 million in 2017 to $3.4 million in 2018. If Trump Organization’s real estate development plans go through, it’s possible that all those jobs he promised Alberdeen in 2005 will come through.
Trump Air – $32 Million
Trump Organization has two planes and three helicopters, but Trump Force One, or the private jet he affectionately calls “T-Bird” is his favorite. He even prefers it over Air Force One, notwithstanding that Air Force One is larger, faster, and higher capacity. Trump notably complained about the bed being too small on the presidential plane, preferring his own private jet’s accommodations. And they are plush. It’s got a cinema system, silk lined bedroom, a guest room, also lined in silk, and a lavish bath, including 24-karat gold, plated fixtures.
Trump purchased the Boeing 757 for $100 million in 2011 and precipitously installed the upgrades. His last name is emblazoned in large upper-case letters—TRUMP— across the outside of the plane, naturally. He used it for his campaign travel. It’s not cheap to fly, it costs about $10,800 per hour. His hopes to use his jet instead of the Air Force issued Boeing 747 fell through after necessary high-tech security systems couldn’t be replicated. In order to increase the size of the bed and update the color scheme of the presidential aircraft to more “American looking” colors, and more to his liking, Trump has ordered two new Air Force One planes which Boeing should complete manufacture of by 2021.
Trump’s Childhood Home
Built-in 1940 by Trump’s dad, real estate developer Fred Trump, the quaint Tudor-style house was their family home until the young Trump was four years old and they upgraded to a larger home. Now it’s a historic relic, or at least a novelty, attracting curiosity and a $2.9 million price tag—far out pricing comparably-sized properties in its upscale Queens neighborhood. So, yes, it’s up for sale! The President of the United States’ childhood home could be anyone’s.
It’s a five-bedroom, 2,500-square-foot darling brick and stucco yellow house with a finished basement and hardwood floors. Inside, you’ll find a library, Trump memorabilia and a cut-out cardboard cut-out of the Prez. For a time, it was available on Airbnb for $725 per night, and the initial listing in August of 2017 ignited a viral craze triggering the media to come herding in droves to the property. I wonder who will end up with a little piece of Americana history?
New York's Iconic Empire State Building
Trump owned half of the Empire State building!.. kind of. . . for several many years. . . From 1994 to 2002, Trump held a 50 percent stake in New York City’s iconic skyscraper, widely recognized as the world’s tallest building after it was constructed in 1931, now the city’s fourth tallest building. What happened was this. A new investor, Japanese billionaire Hideki Yokoi, paid $42 million for the Empire State Building in 1991 and then handed it over to his daughter to own and operate. She proceeded to hook up with Trump, as a native N.Y.C. real estate mogul, giving him 50 percent ownership with no money down—they just handed it to him—in exchange for his commitment to pull off a hostile takeover by breaking the lease.
Trump was convinced that suing the leaseholders, Helmsley and Malkin, for negligence—rats, dark hallways, slow elevators, too many small tenants— would force them to sell their share to the new owners, and he and they would make a marvelous profit, into the billions! Prior to suing Helmsley and Malkin, Trump announced his plan to “restore the Empire State Building to its rightful position as a world-class real estate asset.” The courts ruled against him and he sold his share to the leaseholders. All told, he made $8 million and, even better, he can call himself, “New York’s Native Son” who once owned half of the Empire State Building.
Beverly Hills, 90210 — $13 Million
Trump acquired this fabulous Beverly Hills colonial-style mansion in 2007 for $7 million. He could double his money, but it’s not for sale. Although, the property has been listed and rented out several times. Situated on Rodeo Drive (Location! Location! Location!) the six-bedroom, 6,000-square-foot estate was designed in 1981 by world-renown architect Richard Landry. Trump hardly ever stays there, maybe once a year, choosing to stay at the nearby Beverly Hills Hotel instead. It’s a wonder, His mansion seems to have every amenity: pool, tennis, basketball courts. And it’s a beautiful building, constructed with ritzy Grecian marble and imported Brazilian granite.
The only issue neighbors near the Beverly Hills property contend with is that the hedge around the mansion is too tall. It exceeds the city-imposed limit of six feet, any hedge higher than six feet requires a permit. (Sigh).
The General Motors Building, Midtown Manhattan, NY
The General Motors Building takes up an entire city block of midtown Manhattan, facing Fifth Avenue, Madison Avenue, 58th Street, and 59th Street. The busiest store in the world can be found through a massive glass cube, down a spiral staircase or a glass elevator, into the basement to, you guessed it, the Apple Store. Other high-end retailers take up space, and there’s plenty. The colossal building leases an astounding 1.7 million-square-feet. In 1982 General Motors sold their namesake skyscraper. It changed hands several times, however, in 1998 Trump and insurance company Conesco teamed up to purchase it for $878 million.
Trump chipped in only $11 million for half a stake in the General Motors Building but wasted no time emblazoning the tower with his name in gigantic gold letters. The white marble covered building is 50 stories high and was completed in 1968. Trump cashed in on his investment in 2004, selling the building to developer Harry Macklowe for $1.4 billion whose dramatic real estate loss in 2015 was chronicled by author Vicky Ward’s 2004 book, The Liar’s Bell. Today, the building is worth about $3.4 billion.
Grand Hyatt Hotel, Midtown Manhattan, NY
The historic New York Commodore Hotel located at Grand Central Terminal became the Grand Hyatt Hotel after Trump and the Hyatt Corporation worked together in the 1970s to purchase and renovate the 1919 building with a sleek modern atrium and a glass-sheathed facelift, what would become Trump’s signature mirrored glass and stainless steel façade. It opened in 1980 to wild fanfare, winning the spotlight for the gregarious Trump. It would become the launchpad for Trump’s career as a New York real estate developer. With behind the scenes help from his dad, Fred Trump, Donald won media attention and accolades for being the bold entrepreneur who dared to take on the major project of developing the site and rejuvenating the deteriorating railway hotel and neighboring area with Grand Hyatt’s gleaming high rise.
His vision revitalized a core section of New York City. A significant aspect of the deal Trump brokered was an enormous, 40-year tax break from the city. In an unprecedented move, Trump negotiated this $4 million a year tax break which was the first ever of its kind for a commercial property. It’s cost New York City over $360 million in lost tax revenue to date. Procuring assistance from the government like this would become part of Trump’s strategy, part of the artful nature of his deal-making. In 1976, while this huge deal was going down, Trump told The New York Times how he loves "financial creativeness", saying "There’s a beauty in putting together a financial package that really works, whether it be through tax credits, or a mortgage financing arrangement...” But today, another New York real estate developer has announced plans to demolish the Grand Hyatt and build a bigger, better, more beautiful mix-use project with more luxurious, but scaled back, Hyatt accommodations and new subway access points. The plan, which considerably increases N.Y.C. tax revenue, awaits city approval. Look for the demo crew in 2020.
This towering island luxury property boasts of Trump’s signature resort experience, but technically, Trump International Hotel & Tower Waikiki is not owned or developed by The Trump Organization. Irongate, a Los Angeles real estate company, built the hotel which opened in 2009 and leases the Trump name, it’s a win-win arrangement. Trump likes to showcase his name and name recognition helps fill the 500 ocean view rooms. It’s a beauty.
Five-star, exclusive Honolulu accommodations towering over white sand beaches, where one may indulge in outdoor dining, live entertainment, a private fitness center, a library, the spa, and a private business center, just in case you're forced to go to Hawaii on a business trip.
Maison de L’Amitie, Palm Beach FL
Trump snagged this oceanfront mansion at an auction in 2004 for $41.35 million. Reportedly “gutting it” and installing upgrades and renovations, he flipped the beachfront palace and sold it to Russian billionaire Dmitry Rybolovlev in 2008 for a record high $95 million. The most expensive residence, ever.
By 2016, Rybolovlev decided the ocean view property itself is more valuable than the 60,000-square-foot, 18-bedroom, 3-guest house complex named Maison de L’Amitie and decided to tear it down. But Maison de L’Amitie translated to the house of friendship, was lavish, including a grand ballroom, diamond and gold fixtures, and construction of marble, granite, and mahogany, giving the property a luxury-centric atmosphere. Rybolovlev never lived at the mansion and visited it only once. After the 2016 demolition, he divided up the property into two lots. He sold both, $34 million for one and $39 million for the other, $71 million total for a slice of prime Palm Beach coastline.
More About Bedminster
Located on the heart of New Jersey’s farm country, it’s a beautiful destination. Ivanka Trump held hers and Jared Kushner’s wedding there. Events at the Grand Ballroom, with exquisite floor to ceiling sprawling windows offering never-ending views, or at the classy main clubhouse, a restructured 1930’s Georgian Manor, are nothing short of stunning. The magnificent Manor offers several indoor and outdoor areas for family dining, après golf, or any occasion; accommodating up to 300 guests.
Trump National Bedminster is a world-class golf course, rated among the top 100 golf courses in the world. Designed and built by the legendary golf course architect Tom Fazio, it features two 18-hole Heathlands style courses, the newest opened in 2008. It is scheduled to host the 2022 PGA Championship and costs $350,000 to join. It’s a drop in the bucket for some of the celebrities and political elites who often attend, Rudy Giuliani, President Bill Clinton, and former Yankees manager Joe Torre, to name a few. Membership includes use of the Heli-pad, in case the 45-minute drive from N.Y.C. is too long.
The Bachelor Pad
Just imagine Donald J. Trump in the ‘70s. His silver chauffeured Cadillac with custom plates is pulling up to the Phoenix apartment building on the Upper East Side. He’s worth more than $200 million. Tall, blonde and 30, he’s taking in panoramic views, punctuated by the Empire State Building, as he heads out to meet the driver. On the elevator descent from his Manhattan penthouse apartment, he’s thinking about real deals he’ll land that day. He exits the building and makes his way to the car, climbs in and reaches to make the call on one of the world’s first car phones. When his driver returns him at the end of the business day, he prepares to chill at only the ritziest clubs and date only the slinkiest fashion models.
He’s on the cusp of national distinction, becoming a media darling with a flamboyant and brash personality to match. And it all started in his luxury apartment at the top of The Phoenix Building, an architectural gem designed by the celebrated Every Roth firm.
The Adelaide Hotel Toronto, Canada The St. Regis Toronto
First, in 2012, it was called the Trump International Hotel and Tower Toronto, in name only, and by lease. Then it became The Adelaide Hotel Toronto for a few years, and now, finally, it’s The St. Regis Toronto. Sometimes, the “Trump bump” that comes with having his name emblazoned atop high rise buildings is not an added value. This is exactly what happened in Toronto. The real estate deal he wrangled to build The Adelaide condo complex was already contentious with Canadians.
All of the investors in the residential tower lost money, except Trump. So, when he became President of the United States, protests increased. When he discriminatorily banned traveling to the U.S., he crossed a line and, in 2017, the letters of his name were gradually extricated from the tower. They started with the “M”.
Ivanka Trump’s Trump Park Avenue Home
In 2009 Jared and Ivanka joined their lives at Trump National Bedminster Golf Club in New Jersey. No cost was spared. Her gorgeous gown rang up to $50,000 itself, with an added expense of $220,000 to adorn with jeweled accessories. They would then move into their starter home, a 4,200-square-foot, four-bedroom spread at Trump Park Avenue tower on the Upper East Side in 2011. With a darling nursery in one of the rooms, they set off on building a family.
The penthouse was theirs for about $10.2 million. The stylish digs, designed by Manhattan decorator Kelly Behun, were featured in Elle Decor, but by now they’ve relocated the family to D.C., obviously.
The Hotel St. Moritz Investment
Trump bought the St. Moritz, another Emery Roth design, in 1982 for $72 million and sold it for $180 million in 1985. With major real estate investors vying for the Hotel St. Moritz building and property, it seemed like a huge loss for Trump when he had to sell it. Although he really wanted to develop the property next to Central Park with classier digs and the modern mirrored-glass and stainless façade and was reportedly livid when it was sold from under him, in essence, he flipped the property and more than doubled his investment when he sold it to Australian yachtsman and brewery magnate, Alan Bond, for $100 million more than he got it.
In 1997 he hoped to get a piece of the renovation project once more, but it was sold from under the investors to another investment group who partnered with the Ritz. The building was gutted and remodeled in 2002, transforming it into The Ritz-Carlton New York, Central Park with the top eleven floors available as sprawling penthouse apartments.
Maryanne Trump Barry’s Mar-a-Lago Beach House
Next door to Trump’s Mar-a-Lago golf resort lived his older sister, Maryanne Trump Barry. Maryanne, who served as a federal appeals judge, had a lavish 8,300-square-foot, 8-bedroom beachfront home on the golf course, but her nephews, Don Jr. and Eric, took it off her hands recently. The company they purchased it through paid $18.25 million for the estate home. With ceiling to floor windows overlooking the pool, views of white sand and the Atlantic are to die for.
She purchased the estate in 2004 for $11.5 million. It must be nice to have real estate tycoons in the family!
The Plaza Hotel, Manhattan, N.Y.C.
Trump truly adored owning this building. And, why not? It’s an American icon immortalized in those darling Eloise children books and by the Beatles’ stay for the 1964 U.S Beatlemania premiere. The Plaza even cameos in the quintessential American novel, The Great Gatsby. It represented power, wealth and high society. Trump treasured The Plaza, he infamously called it a “masterpiece,” “the Mona Lisa,” and so he didn’t even peep after losing $550 million and having to file for bankruptcy. Trump bought The Plaza for $390 million in 1988 and precipitously appointed Ivana Trump president of the luxury hotel. He admittedly overpaid to acquire the N.Y.C. iconic building, pouring more money into renovating it, but the income didn’t pay the bills.
It wasn’t the only investment glitch at the time, and the Trump Organization briefly collapsed under $2 billion in debt by 1990. Ivana and Donald split by 1992. After selling his share in 1995, things started to pick up for the Organization again. At the end of the day, all he has left of The Plaza is his function as a minority partner.
Ivana’s Upper East Side Townhouse
Marrying the ostentatious real estate mogul, Donald Trump, in 1977, Ivana was raised in opulence and cultivated for extravagance. The Czech-born diva took to the lifestyle like a fish to water, flamboyantly treasuring her lifestyle as Trump’s wife—model, socialite, fashionista. That ended when a Washington Post columnist approached Ivana Trump and informed her of her husband’s unfaithfulness. With the $25 million settlement, she picked up a swank Upper East Side townhouse that has twelve, or fifteen, bedrooms, she’s not sure. . . One of her favorite rooms is the leopard print room where she takes in some lounging time before heading off to the office, a few flights down.
She has a leopard print room in all over her abodes but splits her time predominately between N.Y.C., Miami and her place in the South of France. She likes to stay local because she’s digging her new “Glam-ma” lifestyle, as her nine grandkids call her. She and President Trump are still in contact, speaking once a month. Truth is, Ivana was the one who broke the news to him last year about Vanessa, wife of Don Jr.’s five children, filing for divorce due to an extra-marital affair. She said he was not happy about it, and she’s sad about it herself. However, wondering if Vanessa couldn’t forgive Don Jr., she told People, in classic Ivana vernacular, “[... .] I honestly don’t know that many men who can keep their zippers up.” As for her opinion on politics and family, she thinks Trump shouldn’t run for a second term and says politics are a “dirty” business.
Trump Bay Street, Jersey City, NJ
Trump Bay Street is an upscale, 50-story residential tower erected across the Hudson River with views of Lower Manhattan. It’s related to Trump in name only, only under license does it represent Trump, neither does The Trump Organization have any stake in Trump Bay Street. This did not prevent peeved protesters from loitering in front of the tower with the president’s name on it in 2017. Meanwhile, Jared Kushner Companies, who hold a 12.5 percent share in Trump Bay Street, helped fund the project by hooking up their foreign investors with a $50 million subsidized federal loan-rate, ironically citing the property’s close proximity to the area’s low-income poverty district.
Kushner Cos. also procured a five-year tax break from the city for their investors. The luxury apartment building which opened its doors to wealthy renters in the fall of 2016, is located adjacent to its twin, the Trump Plaza apartment tower, in name mostly, which was completed in 2008. Jared, Ivanka’s husband, is now a senior adviser to Trump. Due to this new role, Kushner has divested himself of many Kushner properties, but remains involved with Trump Bay Street, holding a two percent stake.
Trump International Hotel Las Vegas, Las Vegas, NV
Las Vegas. This is where Trump’s brand of glitterati extravagance thrives. The Trump International Hotel also accommodates over a thousand ultra-luxury condominiums, including 50 penthouse suites, where tenets live like VIP guests amongst an ambiance of glamour, glitter, and gold with views of the strip and the high-rolling excitement bustling around the epicenter of the entertainment hub of the world. Jutting into the sky, the golden glass tower, reflecting its view, topped in a sleek stainless strip with bold light gold letters just as high—TRUMP—his name headlines the view atop the city’s tallest residential building. Rising 64 stories, making its elegant mark on the city’s skyline, the property is not exactly on the strip, but you can take a shuttle or lavish in white-gloved doormen valeting your car.
According to The Trump Organization’s website, amenities are “beyond world class.” The 640-foot tower opened in 2008. A matching tower was in the works, but the recession and the financial implications coming out of the 2008 market crash slowed the rental and real estate market. The plans are officially on hold. The point, in fact, Trump International Hotel Las Vegas is one of Trump’s most profitable investments since becoming president began to ding his trademark name value. At Trump International, Las Vegas, units are selling. Not only that, they’ve sold for 11 percent higher than asking price!
Trump Hollywood, Hollywood, FL
Here’s another real estate investment that went sour for Trump but yet boasts his name. In 2010 the property was foreclosed on his, and his partner’s, investment. Barely 15 percent of its units sold that year, and it knocked him out of the super-luxury, seaside condominium building deal. The building, built in 2012 by Related Group, has a prime destination and residences sprawling from 2,000 to 5,000 square feet of indoor space.
Views and modern amenities are top notch. Tennis courts, oceanfront cabanas, 24-hour concierge services top the list. Today, Related Group owns the building.
Ivanka’s and Jared’s D.C. Digs
Moving closer to the action, as the two have become a power couple from inside the White House, Ivanka and Jared left their N.Y.C. penthouse and moved into this beautiful colonial 1923 Waddy Wood designed the mansion in the Kalorama section of Washington, D.C. in 2017. Looking like a Beautiful Homes and Gardens pinup, the property underwent indoor modernization filling the 7,000-square-foot home with sleek and contemporary, light and airy ambiance.
The upgrades were finished in 2014 by renowned architect Christian Zapatka. He renovated the six bedrooms, six (and a half) baths, five fireplaces, and the outdoor entertaining terraces. Rumor has it the Kushner’s are crammed into the place and are looking for a larger spread.
A Marla Maples Former Home
Donald Trump’s second ex-wife and mom of Tiffany had some pretty stylish digs. Though modest and scaled back compared with first wife, Ivana, Marla shuttled back and forth from her glitzy residences during her marriage. She leased a sleek East Side sublet for the times she was on the East Coast, and this exclusive Century City, luxury condominium, chock-full of upscale amenities, while on her own in California, when she had time to commit to her aspiring movie star career.
Other times, preferring to be clad in a more jeans-and-T-shirts style, she would weekend on Martha’s Vineyard with hubby, or stay a couple of nights at the high-rollers’ suite in Atlantic City’s Trump Plaza, sometimes chilling with the big “D” at the three-level penthouse in Aspen for $10,000 per week, helicoptering and limo-chauffeuring between.
Ivana’s Upper East Side Townhome, Part II
Ivana Trump’s classy spread is more lavish than you know. Inside you will find this elaborate stairway, an original fixture of the seven-story townhome that provides her a two-flight, curving commute down to the office. Ivana had them redo the ornate rod-iron and gold railing, and then she had artists flown in from Italy to paint a French-Roman garden scene mural which curves with the wide, magnificent staircase.
When she bought the place, she had to gut it. The plumbing was bad, the electricity was nonexistent, the place had been vacant for 12 years, so she ripped everything out and created a personal masterpiece out of the 1924 vintage townhouse. There’s plenty of room for her kids, Ivanka, Donald Jr., and Eric, to visit. Ivanka and her “glam”-kids stay often. And there’s a fireplace in each of the 12 – 15 rooms, the master suite features a glittering gold-embossed mantle and front decor. The original townhouse walls were decorated in a Chinese-style mural. Ivanka had them painstakingly restored by artists referred to her through connections at the Metropolitan Museum of Art. When it comes to gold and diamonds, there can never be enough for this Czech-born socialite! Her dining room is punctuated by an enormous chandelier, imported from Italy. The top floor of the townhouse, formerly three separate bedrooms, is converted to a personal gym with mirrored walls and state-of-the-art equipment. Another feature of extravagance, a must-have in this chic pad, is this room. It’s like a golden-wallpapered, walk-in closet that is the size of a large bedroom, adorned with crystal chandeliers and walled mirrors are the perfect dressing room for this stately fashionista. The lap of luxury.
The original master bedroom walls were decorated in a Chinese-style mural. Ivanka had them painstakingly restored by artists referred to her through connections at the Metropolitan Museum of Art. When it comes to gold and diamonds, there can never be enough for this Czech-born socialite!
Her dining room is punctuated by an enormous crystal chandelier, imported from Italy. The top floor of the townhouse, formerly three separate bedrooms, including Don Jr.’s, is converted to a personal gym with mirrored walls and state-of-the-art equipment.
Ivana’s Walk-In Closet
Another feature of extravagance, a must-have, in this chic pad, is this room. Located on the fifth floor, it’s like a golden-wallpapered, walk-in closet that is the size of a large bedroom. “My closet,” Ivana describes, “goes on and on and on. I call it Indochine because, by the time you get to the end of it, you might as well be in another continent.”
Gorgeous too, adorned with crystal chandeliers and walled mirrors, the perfect dressing room for this stately fashionista. Living in the lap of luxury.
Trump Co-Produced Broadway Comedy Paris Is Out!
Not all of Donald Trump’s business ventures have been in real estate. When he was president of The Trump Organization before handing the financial behemoth over to Don Jr., and Eric, he commanded over something like 500 businesses. From casinos, golf courses, and residential property investment, his success has thrived to wild heights, crashed flatly into bankruptcy and spiked back up again. Some of his efforts at diversifying have included an endeavor to own a USFL football team, and niche, obscure enterprises like the marketing of gourmet steaks.
One of his first forays outside of the mainstream business class and into the arts and entertainment arena was an undertaking to produce a Broadway hit. He was only 23 years old with graduation money from dad for his graduation from Wharton School of Business burning a hole in his pocket. He wanted to make it big, quick, and tapped David Black, Broadway producer, offering to finance his next production. Black’s 1970 Broadway comedy Paris Is Out! starring Molly Picon made it to the theatre in N.Y.C., and precipitously tumbled into obscurity. Ultimately, Trump paid $70,000 to be called “co-producer” of a Broadway play.
The Trump Ice Brand
Trump Ice, the bottled water brand, was discontinued in 2010, but it had an interesting ride. It started out as personal water bottles available to guests at his worldwide Trump hotels, resorts, casinos and residencies, and ended up being heavily marketed on The Apprentice, by Trump himself. In 2003, the water bottles were retailed at specialty grocery chains, and the product push began. Kelly Perdew, a contestant on The Apprentice 2 won the reality-show marketing competition and ran the Trump Ice line for a short while before it went out of business.
Mountain Spring Waters of America, a New Jersey and New York company distributed Trump Ice, while Trump called it, “the purest, best-tasting water you can imagine.” It was sourced from Vermont and bottled in New York.
The USFL New Jersey Generals
In 1983, Trump was hitting his prime. At 37, he had made his mark as a New York City real estate mogul, he had major plans in the works for Atlantic City and he was looking for new and exciting investment. He loved the media attention, saying, “I hire a coach for a football team and there are 60 and 70 reporters calling to interview me.” Hiring billion-dollar business managers didn’t have the same effect, he noticed. So that’s what he did. He went out and bought the floundering New Jersey Generals football team and flipped the organization into the best team in the league. He paid $9 million for the United States Football League (USFL) franchise team. He hired former NFL greats, with great contracts. He hired former New York Jets coach, Walt Michaels. In 1985 he signed Doug Flutie, a Heisman Trophy quarterback. Two years later the league was dead.
A contentious media and court battle between the NFL and the fledgling spring league eventually killed the promising USFL franchise. Year-round professional football was off the table. Trump was used as a scapegoat. Blame Trump. All he did was make the New Jersey Generals great again. (There were some backdoor accusations about Trump trying to have it both ways and bring the Generals into the NFL).
His Sentient Jet, AKA Trump Jets, Is Geared Towards High-Net-Worth Individuals
In 2008, Trump attempted to snug up to an airline venture and officially partnered with Sentient Flight Group, an aviation company that provides world-class, private jet services. The business arrangement Trump brokered offers the option of luxury-chartered flight access to patrons and residents of The Trump Organization properties.
Commuting by private jet is so much more convenient and dignified. Now that’s an amenity!
The good news is, Trump Vodka, in its sealed bottle, is priced as high as $1,000 on eBay. The sad news is, as told by Bloomberg Businessweek in April of 2016, the branded, distilled spirit is “On the Rocks.” Trump Vodka was supposed to be big, great and beautiful. Trump’s trademark marketing of his name kicked into high gear in 2006. Vowing to every camera and mic he met that the next hottest drink would be called a T&T, a Trump and tonic, he fully expected the brand to nudge into Grey Goose’s top shelf space. A bottle of Trump Vodka out-priced Absolut at $33 a bottle. If that wasn’t high end enough, a $100 edition, embossed with a 24-karat gold-leaf label, hit distinguished clubs and clients that same year. In 2007, marketing seemed to be paying off with the sale of 40,000 cases of Trump Vodka.
And then the overextended story, trailing into inescapable debt. The distillery went bankrupt in 2010, and partner Drinks America went belly-up in 2011, selling its assets to another adult beverage company. In Israel, however, Trump Vodka found a distributor, much to Trump’s malign for missing out on sales, but it’s not exactly the same, it’s produced in Germany. The original product marketing detailed a five-time distilling process of select European wheat at a Dutch distillery. It’s sold only once a year, as kosher, for the Passover holiday. A reporter from the Jerusalem Post observed that three sampled bottles were not, in fact, kosher. Trump probably gloated to Orthodox Jews that his brand is kosher.
Trump Fragrance – Success and Empire
Here’s another tale of Trump’s role of becoming President of the U.S. hurting his bottom line. Nike and Macy’s left him in N.Y.C. retail, and, just the same, Macy’s, its exclusive seller, and Perfumania distanced itself from the Trump brand by discontinuing its sales and production of his bottled scents. Macy’s also booted Trump out of the menswear department, discontinuing the Trump line. Three weeks after announcing his campaign, a publicist for Perfumania announced it was cutting ties with the polarizing businessman turned politician.
The Trump Success fragrance brand was launched in 2012 with enticing fresh scents of juniper, red currant and coriander. Empire fragrance marketed in March of 2015, just ahead of his presidential bid announcement, emanated natural scents like peppermint, chai, and apple. The Trump name doesn’t guarantee success, even when it’s called Success.
Trump as Mike Tyson’s Financial Adviser
Another time Trump got involved with the sports business was in 1988 when he promoted a boxing match between the indomitable Mike Tyson and boxer Michael Spinks. Tyson dropped the undefeated heavyweight in a 91-second knockout. Significantly, the fight cross-promoted Trump’s business as well. Taking place near Trump Plaza Hotel and Casino in Atlantic City, N.J., Trump boasted of the $11 million billing for the live and pay-per-view event, the most expensive ever in boxing history.
A couple of weeks after Tyson’s astounding victory, Trump announced he was “charitably” becoming Tyson’s career advisor. Trump called a press conference to say that any income he received from the arrangement would go to his personal charity, the Donald J. Trump Foundation, (another promotional point) for AIDS, cerebral palsy, multiple sclerosis and helping the homeless. The only problem is, Tyson didn’t pay up. A few months later, the Donald penned a letter to Tyson requesting he kindly pay the organization the $2 million that was billed for Trump’s assistance with legal services against boxing manager Bill Cayton’s excessive fees. No response. They remained friends and Tyson endorsed the presidential bid in 2015.
The Macy’s Backstory
The Trump Organization and Macy’s department stores teamed up in 2004 to sell men’s clothing. The line which featured high-end dress shirts, ties and accessories were promoted by Trump himself, appearing in several Macy’s TV commercials. In 2015, all that changed. Citing his racist rhetoric, referring to him calling Mexican immigrants “rapists,” “drug dealers” and “criminals,” Macy’s announced they were discontinuing his line of menswear at their stores. In deference to their clientele, Macy’s published the following statement: “Macy’s is a company that stands for diversity and inclusion. We are disappointed and distressed by recent remarks about immigrants from Mexico.” Trump fired back with a less than classy response accusing Macy’s of supporting illegal immigration.
The menswear items may be found on Amazon and the Trump website, but all ties to the department store giant are cut. The store has not, on the other hand, cut ties with Ivanka Trump’s fashion line, and continues to carry the clothing with that particular Trump label. Men’s wear, another failed Trump Organization venture.
Trump Home products launched in 2007. It partnered with such brands and retailers as, Lexington Home, Serta, Macy’s, Wayfair, Lifestyle, Bed Bath & Beyond, Bellacor, Sears, Kmart, and HSN. Each company has since cut ties with the Organization. Many cited offenses to the aggressive and polarizing 2016 campaign, while others discontinued their contracts without a stated reason.
Serta Mattress and The Trump Organization’s brand partnership was extensive from 2009 to 2015 until Serta allowed their licensing agreement to expire with the following statement: “Serta values diversity and does not agree with nor endorse the recent statements made by Mr. Trump.”
This business barely lasted a year before going bad. Advertised as “the best of the best,” and called, the “world’s greatest steaks” by Trump, the meat, distributed by Sysco, the fast-food supplier behemoth, and sold only through the trendy luxury The Sharper Image catalog and website, the overpriced steaks did not sell.
Even after contestants on Trump’s reality TV show, The Apprentice gushed over the best steaks in the world, they “... .literally sold almost no steaks,” according to The Sharper Image CEO Jerry Levin. The business venture was announced in 2007, The Sharper Image discontinued the product after only two months. A total flop.
Trump’s television Los Angeles based production company was launched in 2004 with The Apprentice, a TV program filmed inside the Trump Tower a few floors down from his uber-luxurious penthouse mansion in order that his appearances would be more convenient. In 2008 the company produced Celebrity Apprentice. And, until 2015, the media company televised the Miss USA and Miss Universe pageants.
It also produces television shows, The Ultimate Merger and Pageant Place. Many viewers are unaware of the Trump association with some of its programs. The company had a value of $15 million in 2015.
Trump Model Management, A.K.A. “T Models”
The Trump Organization announced the phasing out of this company in 2017 following Trump’s inauguration as U.S. President. Founded and owned by Trump in 1999, the laundry list of legal suits and allegations against the company by the models may have had something to do with the abrupt shuttering of the agency.
In 2016, a California Senator called for an investigation into the company’s hiring practices. Behind the scene boycotts of the company by models who questioned the ethics of politician Trump also complicated the relationship. On the upside, Trump Model’s greatest contribution was its division of Legend models in 2012 which revived interest in models over 40.
Trump demonstrated his dearth of integrity and his categorical disregard for ethics in 2004 when he plowed through the New York State Education Department’s (NYSDE) admonition that opening Trump University was in violation of state law. Unauthorized, unaccredited, operating without a license, Trump went forth with his latest niche business enterprise—ripping off the most vulnerable amongst us, students, in other words, folks just trying to make it in this world.
Initially partnering with Michael Sexton and Jonathan Spitalny, who approached him to sell asset management courses, Trump overtook the operation taking a 93 percent ownership. With a sales strategy akin to timeshare sales, interested folks showed up to receive the free spiel, hoping to learn more about the Trump-brand school, but instead got bombarded with a hard sell for their 3-day Trump University workshop that was a $1,495 scam. The lawsuits started there. Two class action and a third individual lawsuit were filed in New York State court for illegal business practices against Trump with reasons ranging from racketeering to false claims. When the Deputy Commissioner for Higher Education, Joseph Frey, sent a letter to Trump in 2010 reiterating NYSDE’s admonition that the use of his use of the word “university” is in violation of New York Education Law. Trump responded a few months later by renaming Trump University. Henceforth it was called The Trump Entrepreneur Initiative. The State of New York responded two months later with a $40 million civil suit against Trump’s school. In October of 2014, a New York judge found Trump guilty and personally liable for operating without a license. Trump uncharacteristically settled three of the lawsuits just after his election in the fall of 2016 for $25 million.
It took Trump about four years to run this company into the ground, no pun intended. In 1988, Trump purchased the Eastern Air Lines Shuttle, a shuttle service offering hourly flights between N.Y.C., D.C., and Boston since 1961, for $365 million. It never turned a profit. High debt, spikes in fuel prices and failing to impress existing customers landed The Trump Shuttle into airline company oblivion as Trump was forced to default on his loans. In 1992, Trump Airlines ceased to exist, and the company was turned over to creditors.
The shuttle service originally serviced passengers with a no-hassle, no-frills, inexpensive commute without seat assignments, reservation, check-ins or boarding passes; a simple, convenient way to hop around the East Coast. When Trump purchased the company’s fleet, he gutted them, obviously installing chrome seat belts, maple-veneered flooring, and, standard, gold-plated bathroom fixtures. His additional VIP touches weren’t worth it to many customers, a stream of paying passengers began to abandon ship. Sales dropped, prices rose.
Tour De Trump
Many a cycling enthusiast agreed that an American cycling race was a long-neglected undertaking. So, one day, inspired by fellow CBS sports reporter John Tesh’s idea that America needed a Tour, Billy Packer, CBS basketball announcer, approached Trump in Atlantic City with a sponsorship role in an East Coast cycling race idea. Trump was very interested and took them up on the plan. Fully invested, he named the race Tour de Trump. In May 1989 the event premiered. With a prize of $250,000, many big names showed up for the race, including Lance Armstrong who won it twice. The route twisted and turned through cities and small towns for 837 miles on the route from Albany to Atlantic City. The route was noticeably personally mapped out by Trump. All the way back in the late ‘80s, Trump had already become a polarizing political figure. Protesters gathered at the finish line with signs like “Fight Trumpism,” and “The Art of the Deal = The Rich Get Richer.” Even New York City Mayor Ed Koch, who once called Trump a “one of the great hucksters,” protested by staying home from the Manhattan leg of the race. As a business venture, it failed.
In two years, Trump was forced to sell to DuPont who became the main sponsor. With a lot of 20/20-vision irony looking back, Trump, who was asked why he didn’t call the race Tour de America in order to develop an event that parallels the preeminent Tour de France, responded, “We could if we wanted to have a less successful race. If we wanted to down-scale it.” The entire Tour, formerly de Trump and then de DuPont, was eventually discontinued in 1996. Trump was getting a reputation for ruining great projects with his involvement.
Miss Universe, Miss USA, and Miss Teen USA Beauty Pageants
When Trump owned the Miss Universe Organization, which includes Miss U.S.A. and Miss Teen U.S.A., it was a hands-on business enterprise. For 20 years he operated the pageants—from 1996 until he was forced out by NBC in 2015. His routine, on pageant days, which he personally attended, included mingling amongst the young women as they rehearsed their final routine before entering the stage, chatting with them and shaking hands with each contestant. In a 2005 interview by Howard Stern, Trump bragged about this exclusive perk, “I’ll go backstage before a show, and everyone’s getting dressed and ready and everything else.” Going on about the access he’s entitled to, “And I’m allowed to go in because I’m the owner of the pageant. And therefore I’m inspecting it. . . ‘Is everyone OK?’ You know, they’re standing there with no clothes. And you see these incredible-looking women. And so I sort of get away with things like that.”
Girls and women complained about Trump’s intrusions on several occasions. In 2015, during the Trump campaign, NBC, who had produced the televised pageant shows since 2002, along with Univision, ended its business relationship with the Miss Universe Organization due to Trump’s negative political opinions. Until 2015, Trump Productions, The Trump Organization’s media company, televised the Miss USA and Miss Universe pageants. Trump tried to hold onto the pageant by buying NBC’s stake but had to sell to a talent agency and entertainment cooperative. His racist comments about immigrants and Mexicans, again, caused him to lose one of his coveted investments.
The Donald J. Trump Foundation
Trump had not contributed to his charitable organization called the Donald J. Trump Foundation since 2008. This, despite the fact that that proceeds from the sale of his book, The Art of the Deal, was supposed to be donated to the organization that he founded in 1988; all the while he mercilessly markets the book and his deal-making prowess. A notable donation came from Linda and Vince McMahon of World Wrestling Entertainment after Trump appeared at one of their WrestleMania gigs in 2007.
They poured a generous $5 million into his foundation. One reason Trump hates the Washington Post (besides that time its reporter narc’d him out to first wife Ivana about his affairs) is that it’s been reporting on the foundation’s ethical violations such as self-profiting from a 501(c)3; making political donations, using funds to settle property lawsuits and tax evasion. Under scrutiny and scandal, the Trump Organization was forced to shutter the charitable foundation last year, a week before Christmas, when his lawyers reached an agreement with the New York attorney general. The organization has given away $19 million to various organizations and causes since its inception.
The Trump Brand – $170 million
Forbes estimates Trump licensing and hotel management, the branding of “Trump,” is worth about $170 million to The Trump Organization; noting, however, that the Trump brand appeal seems to be fading, most notably in N.Y.C. and Toronto. The Trump Organization, for their part, is ahead of the curve. They’ve introduced new brands named “Scion” and “American Idea” as a less polarizing way to sell their products.
Companies are simply not as willing to produce Trump-branded merchandise as they have been. Three years ago, almost 20 companies made Trump-brand merch, today only two international companies produce his namesake products. In 2009, “Trump” was bringing in $215 million a year on such products. In 2017 sales had dwindled to an insignificant $370,000 in licensing deals. The Washington Post has been dutifully reporting on all of Trump’s licensing deals or lack thereof. The Bezos-Trump rivalry keeps getting hotter. Jeff Bezos, CEO of Amazon and WaPo owner is number one on the Forbes 400 list. Trump, substantially lower. No envy there.
The Casino Deals
Trump got into the casino business in earnest in 1984 when Harrah’s at Trump Plaza opened in Atlantic City. In 1986 he bought out Harrah’s stake and management for $250 million, and it came to be known as Trump Plaza. He purchased another building in the New Jersey city from Hilton for $320 million, transforming it into Ivana’s management project they called Trump Castle. But Trump had his eye on an even bigger slice of Atlantic City. His plan was to take over Resorts International, a struggling casino franchise which was the largest landowner in the city.
Its Taj Mahal project, the world’s largest casino, stood partially finished. Trump acquired it for $280 million in 1989, stretching credit and funds for the massive project that opened in 1990. He also picked up the Atlantis, renaming it the Trump Regency. The 1990s recession caused him to lose all but 10 percent in his Atlantic City properties. He stretched his investments too far, and his highly leveraged empire nearly collapsed.
The Golf Resorts – $550 Million
The Trump Organization owns about 18 golf courses and clubs worldwide. Most of them are located in the U.S., however, Trump owns one in Ireland and two in Scotland. Trump’s been wanting to develop the Scotland, Aberdeenshire golf resort, adding to his existing development with luxury accommodations and residences, for a long time. He’s been very patient. In Aberdeenshire, Scotland, however, neighbors have not been supportive, to say the least, and his cavalier attitude has earned him a lot of pushback from the locals. He’s been accused of bullying local residents into accepting his plans. Some felt threatened to sell. He announced to worldwide media that he’s getting rid of one neighbor’s home because it’s ugly. He built a wall and asked neighbors to pay for half.
Recently, the Aberdeenshire Council has been bombarded with a record number of formal letters of objection. Over 3,000 residents have written to the council to lodge their complaint, at exactly 3,026 letters, it’s the highest number in council history. The vote to allow the Trump Organization to go through with its development plan will happen early this year. (It’s rumored that a large percentage of the investment funding comes from wealthy Russians who adore Scottish golf courses after Eric Trump said as much to a Fortune golf writer while golfing with him in 2013. He since denied saying that, calling it “fake news”). Trump also rubbed the Scottish the wrong way by using an unregistered, possibly plagiarized, coat of arms in his resort branding. The heraldic officials in Scotland were not pleased. All coats of arms must be registered and approved by the Court of Lord Lyon, he wasn’t. They shouldn’t feel offended, he never licensed Trump University either.